Is Jack Connors the Last King of Boston?

THE LUMINARIES WHO DOMINATED the city during Connors’s lifetime — Billy Bulger, Tip O’Neill, Ted Kennedy — were all politicians. In a way, Connors is one, too. He’s always approached the city’s corporate culture as a ward boss might his constituents — by getting in front of as many people as possible.

From there it was just a matter of building relationships. Connors was never an ad man per se. He’s the first to admit he knows nothing about creating a good ad. But like a good politician, he could sell himself. And once people bought that, he gave them even more than he promised. He gave them his time and, as the years progressed, his myriad connections. His longtime friend and former client, one-time John Hancock CEO David D’Alessandro, puts it this way: “He got close to people and then he realized that what interested executives were their own careers, the charities they gave to, their families. And he would always find a way to get close to those issues.… Jack kept some clients longer than anybody else ever did. The work was good…. The work was fantastic. But you can get that work from somebody else. But you don’t let them go because you need Jack. Jack helps your career. Helps your family.”

This practice of intervening — for the greater good, for Connors’s own (for both) — has been a hallmark of his career. His relationship with D’Alessandro is a case study in Connors’s blurry line between good deeds and good business. John Hancock had been a Hill Holliday client for a couple of years when D’Alessandro’s mother died in 1986. D’Alessandro told no one but his boss, and drove the four and a half hours to upstate New York, where he’s from. There were two wakes for his mother, one in the afternoon and another in the evening, and in between D’Alessandro went with two of his aunts to a local Italian restaurant.

There, sitting at the bar, was Connors. He’d called D’Alessandro’s office earlier that day and coaxed his secretary into revealing the reason D’Alessandro was out of the office. Connors rented a private plane and had the pilot land in a nearby airfield. For two hours at dinner, Connors sat between D’Alessandro’s two aunts, making them giggle at his stories. “He took this pressure off of me, having to deal with my mother’s death,” D’Alessandro says. He never forgot it. Neither did his aunts. For years they asked D’Alessandro about the “nice Irish man.”